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KMID : 1059519960400100663
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Journal of the Korean Chemical Society
1996 Volume.40 No. 10 p.663 ~ p.669
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Kinetic Studies on the Nucleophilic Addition of Thioglycolic Acid to S-Phenyl-S-vinyl-N-p-tosylsulfilimine Derivatives
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Kim Tae-Rin
Han Man-So
Pyun Sang-Yong
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Abstract
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The rate constants for the nucleophilic addition reactions of thioglycolic acid to vinylsulfilimine(VSI) derivatives(p-OCH3, H, p-Cl and p-Br) were determined by an ultraviolet spectrophotometric method, and rate equations which can be applied over a wide pH range were obtained. On the basis of rate equation, general base catalysis and substituent effect, a plausible addition reaction mechanism was proposed: Below pH 3.0, the reaction was proceeded via the addition of neutral molecule to carbon-carbon double bond after protonation at the nitrogen atom of the sulfilimine, and in the pH range of 3.0 to 9.0, the neutral molecule and its anion attacked to carbon-carbon double bond competitively. Above pH 9.0, sulfide anion added to the double bond (Michael type addition).
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